


The Chronicles of Some Undead Losers

by Indubitablydumb



Category: Supernatural
Genre: Castiel and Dean Winchester Need to Use Their Words, Chuck Shurley is God, Dad Castiel, Dad Sam Winchester, Dead Dean Winchester, Dead Sam Winchester, Gen, Heaven & Hell, Jack Kline Needs A Hug, M/M, Sam Winchester is So Done, They are NOT in heaven, dad dean winchester
Language: English
Status: In-Progress
Published: 2021-01-11
Updated: 2021-01-12
Packaged: 2021-03-15 17:40:48
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 3,083
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28692633
Author URL: https://archiveofourown.org/users/Indubitablydumb/pseuds/Indubitablydumb
Summary: Dean Winchester knows that something is up the moment he turns up in Heaven-- or, what they want him to think is Heaven. He doesn't know what's going on, but when Sam finally kicks the can, he knows that something is off, too. With repressed feelings in the mix and a few old friends they find along the way, can an old man in the body of a thirty year old, a weary drunk, a just recently resurrected angel, and a bisexual functioning alcoholic work together to save not only themselves but their cosmically powerful four year old son, too?--This fic is based on a couple of theories and ideas I saw circulating Tumblr. I decided that I'd take the ideas people have already given and meld them into a little something of my own. It will circle around deancas, for the most part, but the plot is also a big part of the story.
Relationships: Castiel/Dean Winchester, Eileen Leahy/Sam Winchester
Comments: 3
Kudos: 13





	1. So, We Meet Again

Dean knew the second he'd gotten there that something hadn't been right. That’s arguably why he’d waited so long to make an actual move. 

_ “Time up here, it's… it’s different.”  _ Bobby had said, his gaze seemingly knowing. Maybe it would have been if Dean had been talking about Sam in the first place. No, he knew that something had been wrong because if Cas was truly alive, Dean knows that he’d have at the  _ least _ dropped by to say hello. 

Cas never did let Dean die easy. 

So, he waited for Sam. Which was, by the way, absolute torture. For one; the road he was driving seemed to have no end, no final destination. Sure, it was unfinished, but still-- Heaven seemed eerily empty. For two; why in the  _ world  _ was  _ Carry On Wayward Son  _ the only song playing over and over through every channel on the radio? If he’s supposed to be in Heaven, he should be able to tune into one hit wonders from fucking mars. Even so, it didn't really bother him-- not at first, at least. The song  _ is  _ a classic after all. After the seemingly hundredth time, though, he felt compelled to bash radio in with his head. He opted to just switch it off instead. 

He could instantly tell the moment that Sam had finally arrived. His brother’s presence was a heavy shift in the air around him, and he could feel the difference in the dimension’s atmosphere eating its way to the core of his very soul. 

Meet up with Sam, figure things out. His default game plan. 

He doesn't know exactly how he ended up at the bridge, or how it even got there in the first place. Still, it’s so corny that it serves only as more fuel for his looming doubt. He knows that Sam will pop up here sooner or later, though (why else would the bridge just randomly pop up on the eternal road he just happened to be driving on), so he parks his car and he waits. 

Finally,  _ finally _ , his brother shows. 

“Hey, Sammy,” He says, turning on his heels to face the taller man, who only looks at him and smiles. For a second, Dean wonders if it's actually Sam. He has no reason to believe it's  _ not _ some heavenly charade against his sanity. But then his brother leans over to wrap his arms around him, and as he pats the taller on the back he reasons with himself that, for Sam, it’s been  _ much  _ longer than it has for him. 

“So we really made it, huh? To heaven? Bobby told me the works.” He says, his eyes all doughy. Dean’s lips pull into a tight frown. 

“That's the thing,” Dean says, shifting his weight. “something feels off.”

“Not wasting any time, huh?” Sam laughs, shaking his head so that his bangs fall over his eyes. “So, what is it this time? Heavenly apocalypse number infinity?” 

"Listen, I have no friggin’ clue,” Dean says, feeling a strange obligation to lower his voice.  _ Anyone  _ could be listening in right now. “but everything is just… sketchy. Bobby told you that Cas is alive, right? The dude hasn't even come to see me.” 

Sam furrows his brows. 

“What? I thought he’d be _ pissed  _ about you… y’know.” He says, frowning. 

“Yeah, I’d think so too. Plus, they only play the same song on the radio, and you  _ know  _ how much overplaying songs bothers me. You can drive forever and ever and get completely _ jack _ , and have you seen anyone other than Bobby around here?” Dean swallows, hard, trying to stop himself from sounding like he's on the verge of making tinfoil hats. “Like, come on, where’s Ellen and Jo? Where’s Pamela, and Jess, and… and Ash! Damn, I miss that weird little guy.” 

“You’re right, Dean, that does sound weird.” Sam says with a frown. “How long have you been here? You know, in… in heaven time, or whatever.” 

“Not long. Feels like it's been, what, a week tops?”

“Okay, so, we just got here. Why don't we lay low, do some poking around. We can drive back out to Bobby’s, I guess.” Sam says after a small pause. 

“If he’s even Bobby,” Dean mumbles, opening the car door. 

Sam huffs out a breath, clambering into the passenger seat with frown. 

“ _ If  _ he’s even Bobby.”

\---

“So you're telling me,” Dean says, brow raised. “that you quit the job, had a kid with some random chick you met in a bar, and-- died of old age?” 

“Yeah, that was pretty much it.” Sam says, glancing out the car window. “Why, what did you expect?” 

“Listen, Sam, it’s-- it’s great that you got to see old age, alright? Go team Winchester, sure. But, man, what happened to Eileen? And naming your  _ kid  _ after me? I’m sorry, but that's all  _ kinds  _ of weird.” He frowns, glancing at Sam. The younger shifts his weight. 

“Um,” He starts, his mouth suddenly dry. Why can your mouth even  _ get  _ dry in heaven? “After what happened with Chuck, Eileen didn't really want much to do with me. And about D--” Dean shoots him a look. “My  _ kid _ , I mean. Listen, I didn't think it would be weird when I named him that. I was grieving. But, really, he’s a good kid.”

“Does he know?” Dean asks, raising his eyebrows. 

“Yeah, he knows. I actually brought myself to buy him a set of Chuck's books.” Sam says with a dry laugh. 

“And he  _ read  _ all of them? Jesus.” He rips his gaze from Sam and back to the road ahead of them. “Oh, look. The roadhouse.” He says, lips tightening into a line.

He finds it strange that it had taken him thirty earth years to get to the bridge, but not even a sliver of that time to get all the way back. 

Whatever. 

Bobby isn't sitting outside anymore, so they hop out of the car and decide that just walking in should be fine. It’s not like there's much repercussion, unless Bobby’s in there doing something weird. 

Whatever Dean could even start to picture what could qualify as weird, what they actually find going down in the roadhouse doesn’t even come close to it. Actually, he doesn't even think weird qualifies to define it at all. 

For reasons he can’t even bring himself to figure out, his heart drops. Maybe it's because the roadhouse, even on the inside, looks exactly as it did in life. 

Or, maybe it's the angel with the tousled hair and the big tan trench coat pacing up and down the room like nobody's business while Bobby looks up at him with the most weary expression that Dean has ever seen plastered across his face. 

“I just don't understand,” the angel says, hands jammed inside his pockets. 

“For the hundredth time, I  _ know. _ ” Bobby grumbles, taking a long swig of his beer. Cas turns to glare at the man, but his eyes meet Dean’s and as they linger there, Dean’s heart stutters in his chest. 

He looks… younger. Not dropped-eleven-years kind of younger, but he seems calmer now, and some of the saddened wrinkles around his eyes have retreated. The scenery around Dean tunes out as he looks into those blue eyes, reminiscent of a time where the only thing they really had to worry about was the devil. 

There's a million things he wants to say in this moment, a million ways he’s pictured it going down. A million ways he’s  _ longed  _ for it to go down. But he doesn't say any of them, and he forces all of those scenarios back to the corner of his brain where he’d left them. 

“Cas,” Is all he can say, voice faltering. And then, before he can think it over enough to stop himself, he lunges forward, ignoring the looks Sam and Bobby send him as he wraps his arms around Cas and leans his chin against the angel’s shoulder. He exhales as Cas, even though hesitantly, snakes his arms around his middle. 

“Dean.”

_ Don’t do this, Cas. _

_ Goodbye, Dean.  _

“Cas, man, I-- I really thought I wouldn't see you again.” 

Cas wriggles out of Dean’s grip, moving his hands to rest on his shoulders. For a short, wishful second, Dean thinks that something might happen. 

“You died,” Cas whispers. 

Dean was wrong. 

And, also, what the hell is he supposed to say to that?

Thankfully, he doesn't have to figure it out, because Bobby clears his throat from his seat at the bar and Cas draws back, hands returning to his pockets. He looks at Sam across the room, and Dean wishes he could say that he already misses those blue eyes focused on him. 

“Hello, Sam. It’s been a long time.” 

Sam only smiles. 

“Are you going to tell these boys why you're here, or are we just going to keep yapping out casualties for the rest of eternity?” Bobby says, a brow raised in bitter annoyance. Cas rolls his eyes, but looks back at Sam and Dean nonetheless. 

“I’m sorry that it took so long to reach you. That’s actually the issue. It’s Jack, he… he isn't Jack.” 


	2. Heavenly Resolve

“Wait, what? What do you mean he’s not Jack?” Sam finally asks, pulling out a stool from the bar with an exasperated sigh. Dean feels for him, really. The guy just died and he’s already being dragged into typical Winchester bullshit. The works. 

“I am thoroughly convinced that Jack is actually Chuck.” Cas supplies, his expression solemn, and Dean  _ wishes  _ that he could find it in himself to pay any real attention to what the angel is actually saying. No, instead he’s letting himself indulge in the very  _ presence  _ of Cas. He’s here, he’s  _ alive,  _ and isn’t that really all that matters right now? 

“Well, I can’t say I’m surprised,” Bobby says, voice gruff. “Kid sucks in all that power, something like that is bound to set off a beacon of sorts. An entity like Chuck could probably sniff that out half way across the universe. Not to mention he’s the definition of all-knowing.”

“But he was still Chuck when we left him. And that was  _ after  _ the whole power-swap dance,” Dean says, finally ripping his eyes from Cas to meet Sam’s gaze. 

“I’m assuming that he knew about your plan for his demise. There’s many ways he could have avoided the outcome, but it’s most likely that he was able to possess Jack and shift his consciousness onto Chuck. Therefore when something happened to his vessel, he hadn’t genuinely been in it enough to take the damage,” Cas elaborates, back to pacing up and down the room. Dean frowns. 

“Like a horcrux?” Sam asks, an eyebrow raised. Cas sends him a confused glance. “What,  _ Harry Potter  _ wasn’t in that media download Metatron gave you?” 

“Give it up, Sammy. Nobody else here knows what you’re talking about,” Dean mumbles, walking over to the bar and grabbing a bottle from the shelf. He pops off the cap, taking a quick sniff and wincing at the burning sensation it shoots up his nostrils. Deeming it acceptable, he grabs a tall glass from the cupboard and starts pouring. What are the repercussions if he’s already dead? 

“Don’t do that, Dean.” Cas says, frowning at him from across the room. 

“Don’t do what?” Dean asks, playing along. 

“Drink yourself out of this. It's not going to help you. We need to come up with a solid plan.” Cas says, but Dean is already chugging the liquid like he isn’t going to see tomorrow. Hell, at the rate they’re going, maybe he’s not.

“So,” Sam says, evidently going for a not-so-subtle change of topics. “If Chuck is actually Jack, as of now--”

“--Then where’s Jack?” Bobby finishes, standing up to grab the bottle of alcohol from Dean, who is already pouring himself another glass. 

“That’s what I’ve been thinking,” Cas says, pointedly ignoring Dean and his childish behaviour. “If he’s still in there, Chuck could have warded him from me without my knowing. For all I know, he could be--”

“Dead!” Dean pipes up, but his expression is mostly blank. He’s already wasted. 

“At the least, yes.” Cas says wearily. “Knowing Chuck, he could have snapped Jack out of all planes of existence by now.” 

“Shit,” Sam mumbles under his breath. 

“Well, we can’t do anything with him like this,” Bobby says, pointing over at Dean, who is gulping down the last of his drink. “And Sam, get some rest, boy. I know you just died and all, but you look like shit. There’s a spare bedroom in the back.” Sam pulls a weak smile, nodding. 

“Make sure he doesn’t do anything stupid,” He says, eyeing Dean, who is now staring at the floor with a soft smile. He hasn’t seen his brother this wasted in decades, but maybe he has some heavenly anti-tolerance going on.

“Nothing to worry about. He won’t pull anything on my watch, let alone the angel’s.” He turns his gaze to Cas. “Why don’t you go and take him for a walk? I’m sure you boys have a lot to catch up on.” 

Cas shifts his weight uncomfortably, looking back at Dean. He hadn’t expected to come back at all, and he certainly isn’t prepared to face Dean head on. Not when he knows, now. On the other hand, though, he doesn’t look very bothered by it-- in fact, earlier he’d actually seemed  _ happy _ to see Cas again. So, he shoves down his baggage and nods. It's still Dean, after all. Dead and inebriated, maybe, but still Dean. 

“Dean,” He says, glancing at the door and then back at Dean before walking out. He hopes that he’ll get the hint, but knows somewhere in the corner of his fucked up conscience that even if not, Dean will follow him anyway. 

“Cas-- Cas! Wait up!” Dean says, just barely stumbling as he jogs to catch up with Cas. “Where are you going?” 

“I’m taking you for a walk,” Cas answers quietly, looking around. If not in heaven, where  _ are  _ they? 

“Oh,” Dean says nonchalantly. He’s looking at Cas, now. It's not flirtatious, or skeptical. He’s in awe. He’s  _ awed  _ by Cas’s presence. If it were anybody else, Cas would say that it serves himself right. He  _ is  _ an angel, still. With Dean, though, it's just… different. He almost doesn’t  _ deserve  _ Dean’s attention. “Cas, what happened? After-- after you--” 

“After I was absorbed by the empty?” Cas says, training his eyes on Dean’s. Dean nods, suddenly emotional. “I was down there for a while. The blast of power Jack must have given off, it woke the majority of the angels and demons in the empty’s void, so obviously it wasn’t very happy at the time.” 

“What was it like?” Dean asks, frowning. 

“It was dark. Quiet. Time, it went… much slower. I was there for a couple of days before Chuck resurrected me, but it felt almost like centuries.” Despite the terrible experience he’s now verbally recalling, he seems calm. “What about you, Dean? How did you die?” 

“I killed myself,” Dean blurts, his eyes trained on the ground below them as he walks. “Basically. I saw an opportunity to get out and went for it, more like.”

Cas swallows. 

“And Sam, he--” 

“He was there. He doesn’t-- he doesn’t know, though. That it was on purpose. You’re the only one that knows.” 

Cas stops walking. He places a hand on Dean’s shoulder, frowning. 

“Dean, you can’t expect me to-- to be  _ okay  _ with that.” 

“No, I-- I know. I just thought that I should tell you. You deserved to know.”    
  
Cas exhales, expression growing somber. 

“Why did you do it?” He asks, swallowing down the pit in his throat. He finds it ironic that even though Jack-- no, Chuck-- had returned him to full power, wings and all, he’s still closer to being human in emotional aspects than he’d ever been before. 

“Because, I-- I don’t know. It just felt... it felt wrong, without you. Without Jack. But you most. I  _ tried,  _ Cas, I tried to keep going, but after Chuck-- I just couldn’t go back to how it was, you know?” He exhales shakily, letting himself lean against Cas’s hand. “I know what you said before you-- before you died, Cas, but-- you were wrong. I’m a monster.” 

"No, you don’t  _ get _ to talk about yourself like that. Not when you’re drunk, not when you’re sober, not when you’re dead. I won’t let you,” Cas says, his grip on Dean tightening. “Because you’re wrong. I’m not going to take back what I said. I’m not going to pretend that it didn’t happen. You may not feel the same way, but I love you. I love you when I shouldn’t even be  _ able  _ to love you, when I never even had the capacity to love before you. Your life matters, Dean.  _ You  _ matter. To me, of course to me, but to everybody else, too. And you may be The Righteous Man, and The Michael Sword, but that’s not what makes you important. You matter because you’re  _ you _ .”

Dean trembles, tears threatening to spill, because goddammit he’s intoxicated and he’s  _ dead, _ and this is  _ Cas _ saying all of these nice things to him. Cas, who he’d thought was in the wind. Cas, who he’d thought he was never going to see again. Cas, who he is  _ in love with _ . 

“No, Cas, you--” For a second, Cas thinks he’s going to try and fight him on it again, that maybe he’ll have to actually beat the sense into him. But instead, he gives this shy, teary-eyed smile, and then says, “I love you too, Cas.”

And Cas is on the moon. 

Dean, though, is still a wreck. He’s drained, and overwhelmed. He’d been thinking about this moment for so long, breaking under the looming reality that it would  _ never happen _ . But despite all of the odds, it did. It  _ is _ . 

He shrinks in on himself, and Cas steps forward, taking him into his arms and letting him sob against his chest. He runs his hand up and down the small of Dean’s back, inhaling shakily. They stand there, just the two of them, wrapped in each other’s arms. They stand there as long as they need to, because neither of them can easily accept that this is real. That they’re both here, and they’re both in love, but even so-- 

They’re both in a ton of shit. 

**Author's Note:**

> So, what are ya'll thinking about this one? Writing this is genuinely THERAPY.


End file.
